


Cruisin'

by pleasurific



Series: TW Kink Bingo [2]
Category: Teen Wolf (TV)
Genre: Anal Fingering, Anonymous Sex, Barebacking, Cruising, Exhibitionism, First Time, Fluffy Ending, M/M, Outdoor Sex, Post-Season/Series 02, Public Sex, Rimming
Language: English
Status: Completed
Published: 2018-08-06
Updated: 2018-08-06
Packaged: 2019-06-22 21:45:05
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,802
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15591360
Author URL: https://archiveofourown.org/users/pleasurific/pseuds/pleasurific
Summary: There's a spot out in the woods that's known online as the place to go cruising, the place to meet random strangers for sex. Stiles, of course, finds this more than intriguing.





	Cruisin'

**Author's Note:**

> For Teen Wolf Kink Bingo square "outdoors".

It takes a little work to set up the Jeep the way he wants to. Sure, the back seat already folds away and the tailgate opens, but he struggles to figure out how to keep the window open -- the latch has been broken ever since he can remember. Once he's got it, Stiles pushes away all thoughts of everything associated with Roscoe -- that it was his Mom's car, the time Jackson was knocked out in the back seat, the time Derek almost  _ died _ in it -- and tries to focus instead on what's to come. Or who is. 

There's a spot out by the Preserve, one that he never really went to because of what it is. But ever since he was old enough to snoop and listen in to conversations at the Sheriff's station, he knew about it. Of course at first he didn't understand what it meant, what the officers meant, when they talked about dogging, or when they mentioned not wanting to get the route that would take them by the dirt road in the evenings. Later though, Stiles figured it out, at about the same time that the deputies and officers started being more careful around him with their chatter -- no doubt on the instructions from his father -- Stiles looked up the term online and even found the spot listed on a website's directory. 

It wasn't immediately intriguing. After all, he had his obsession with Lydia, then the whole mess with the supernatural, and somewhere in between all those things, his curiosity got pushed aside. 

But he never forgot it. 

He doesn't make it a point to look up regularly whether the spot is still active, but it never takes him long to venture onto that one particular site when he has a moment to himself, nor to ones like it. Quiet moments when he can research his possible kinks and the temptation of them; when he can sit back in the privacy of his room explore what looks like something he wants to try and what doesn't. Of all the things -- and he has a list now -- this one seems the least dangerous. 

The spot isn't as active according to the website as it used to be, which Stiles figures must have something to do with the rumors of things going the not-fun kind of bump in the night. But that's for the best, really, he thinks as he drives out there. The fewer people know about it and frequent it, the less of a chance there is that he'll be found by someone he knows when he doesn't want it. According to the site, most visitors are from counties around this one, not from the town. The anonymity makes it somehow more interesting too, the not knowing who he's going to run into out there. 

There's a chance that he's going to be interrupted by a phone call from either Scott -- who's spending his summer moping about Allison -- or from Derek, who's still spending his days scouting the woods for Erica and Boyd with whatever help he can get. But Stiles's phone, while he's planning to have it close by, is going to be on silent to prevent unnecessary disruptions to his plan. 

Not that Stiles knows precisely what his plan is. For all that he knows, he'll spend hours sitting in the back of the Jeep staring at the trees, and nothing will happen. That thought is disappointing, but he's not letting himself get his hopes up, since he knows that not many people venture out that way. 

It's also a chance to confirm which way his sexuality is veering. There was no other option than Lydia for a long time, but ever since their venture into  _ Jungle _ , Stiles has become curious about that too. When he was preparing for today, it included imagining things other than the usual straight porn he was familiar with ever since he got internet access and figured out what his dick was for. So right now, his ass is slick with the lube he smeared around it before he left the house, his dick half hard already because of that sensation, and his mind open to, well, anything. 

The Preserve is quiet and the dirt road empty as Roscoe rumbles along, no other cars or people in sight. Once he gets to the right spot and checks the GPS to make sure it’s where he wants to be, Stiles stumbles out of the car and makes his way to the back. The tailgate opens easily -- he had it fixed so he could be sure that it would hold his weight -- and the back window provides a makeshift shelter. above it. 

There's nothing but woods around him when he climbs up, shedding his shirt and jeans once he's in the back. It's not the most comfortable position, but Stiles first stays all the way in the cover of the Jeep's back, leaning against the side, the back seat folded to provide more space. The heat rises fast as time passes so he pulls off his tee and stays in just his boxers, legs stretched across the cargo space. It wouldn't be any different to just driving out to the beach and hanging out in the back of the Jeep if it wasn't for the twitching of his dick under the thin layer of fabric that reminds him that he's here for something else. 

His mind wanders as he waits, soon bringing up thoughts of what might happen. His dick fills as he imagines someone coming up, offering to watch him, maybe to blow him -- both would be a first, he's barely even been kissed, let alone had anything resembling sex. With those thoughts, Stiles tugs the boxers down and wraps a hand around his cock, stroking it slowly as he brings himself to full hardness. He shifts around then, takes his boxers off completely, rests his thighs on the tailgate and his feet dangle almost to the ground, legs spread as much as he can in the limited space. 

He stares out into the forest, imagining someone lurking in the shrubbery, watching him as he jerks off slowly, leisurely. Then, on a whim, he turns around and gets on his hands and knees. He folds one arm underneath him, resting his forehead on it, the other one reaches for his dick and goes back to stroking. This way, his legs are open and his ass up high, the slowly drying lube still damp enough that the breeze blowing around it makes it cool, sending shivers down his spine. 

Stiles wonders how he would look to someone walking up -- ass sticking out of the Jeep, hole open and twitching, the smell of precome spreading around. He imagines someone watching from the woods, jerking off at the sight of him. It's almost enough to get him off, but he holds back, tries to draw it out. 

There's a light breeze around and it makes the trees whisper and the leaves rustle just enough that it makes it easier to imagine someone lurking around, moving closer. It also brushes over his hole in a way that makes him imagine someone's tentative touches ghosting over his skin. 

Suddenly, there's a louder crack, like someone stepped on a twig. Stiles freezes, his fingers tense around his dick, and he wonders if it's an animal passing by or if he's about to get arrested by one of his dad's deputies. There's only silence though for a few beats and he starts to relax and loosens his grip on his cock. Right when he's about to start jerking off again, there's another crack, closer this time, more deliberate, like someone wants him to know what he's not alone. Stiles's asshole twitches and in the silence of the forest he can hear a deep breath. 

He's definitely not alone. He could lift himself up and look who it is, see the person's face, but something about the anonymity is exhilarating. Before he can think about it any further, the deep breaths continue and move closer, until a shadow falls on the tailgate just where Stiles can see. He bends his neck just enough to glance between his legs and spots a pair of jeans tight around muscular thighs.  _ A guy, then _ , he thinks, his whole body trembling with anticipation. The jeans slide down, revealing legs that are covered with hair, tight muscles and a flash of a hard cock between them that almost makes Stiles come too soon. 

Then there are hands brushing over the back of Stiles's thigh, thumbs visible up until they rest just above his balls and then rub higher, just around the edge of his hole. An approving hum is the first noise that the guy makes as he rubs one of his fingers over Stiles's hole, and then there's a breath against it and a tongue and Stiles almost loses it. He drops his hand from his cock, trying to minimize the stimulation -- the sight of the body behind him and the cock pointing between his legs just above the edge of the tailgate enough to push blood down into his own dick. 

He never thought it could be like this, wet and sloppy, his hole being licked and sucked on like the man wanted to literally devour him, the muscles loosening as a tongue dipped into him over and over, so much better than his own fingers. Then there  _ are _ fingers, a gentle touch first, then a press past the ring of muscle and a slightly rough slide because the saliva isn't quite enough. Stiles was prepared for this -- there's a small bottle of lube next to his leg and the flails a hand in its direction. His wrist gets pinned down roughly -- he files the shudder that  _ that _ causes for further study -- and the bottle disappears from Stiles's sight, the tell-tale click of the lid explaining where it's gone. 

The next time the finger dips into him, it's more smooth, the catch of a knuckle barely noticeable as it slips inside him. He feels the tip of the finger brush against his prostate and he keens, arching his back and sticking his ass out more. He feels the second finger poke at his rim, next to the first, then it tugs on the edge until he's clenching before opening up. One finger pulls almost out, then two are pressing in, stretching his rim a little as they push inside, wider than his own when the knuckles pop past the muscle. He lets the sensation wash over him as the man pumps his fingers in and then pulls them out, a slow and tantalizing rhythm sending sparks down to Stiles's leaking cock. Then there's more pressure on the rim as the fingers scissor open, still moving in and out and stretching him. 

Again, he wonders how he looks, how his hole looks to the man who's stretching it, open and wanting, trying to clench down and then opening up like it wants more. Because Stiles wants more, he wants another finger, wants something thicker, something spreading him wide and filling him up. He muffles a moan into his arm when a third finger joins the two, the most he's ever taken until now. His legs try to move, try to spread further, but the back of the Jeep isn't big enough. 

The man seems to notice this and he pulls his fingers out -- Stiles whimpers at the loss, feeling empty and gaping immediately -- then tugs on Stiles's thighs to move him more to the edge. The next thing Stiles knows, he's manhandled so his feet are spread apart and on the warm ground, his torso flat on the back of the Jeep's cargo space and the tailgate, dick brushing against the edge. He doesn't get to think about it though, because the fingers plunge back into him, two and then three, his spread legs allowing for better access. He knows that his ass is now level with the cock of the man fingering him and Stiles tries to arch his back and stick his ass out more. 

When the fingers slide out of him, he whimpers again, but a moment later there's something else pressing at his rim, something blunt and wet and hot. The head of a cock that's being rubbed against his pucker, not sliding in just yet.

"Please," he whines, making an effort to relax his hole as it pulses with want. 

A hum is the only response he gets, then the cock starts pressing forward, into him, stretching him more than the fingers did moments before. The man pushes into him slowly, stopping every second as Stiles clenches around his width. It seems to take forever for the dick to be fully in Stiles's ass, coarse hair scraping against his ass, balls bushing against his own heavy ones. Then the man pulls out and away, his thumbs replacing his cock on Stiles's rim, holding his ass open. 

The next plunge is faster, more decisive, and Stiles yet again keens and whines as the man slides into him until he's balls deep. Then he pulls out again, pauses for a beat as he holds Stiles open before he fucks in. 

"Please," Stiles says again, not caring how desperate he sounds. 

He gets his wish then. His hips are held in a firm grip as he's fucked in a steady rhythm, no sounds other than grunts from the man behind him and Stiles's own moans. 

If he was able to pay attention, Stiles would probably notice that the man is firm but not rough. He'd notice the familiarity of the grunts that are bouncing of the walls of the Jeep. But he doesn't. All his brain can process is the stretch of his ass, the grip of hands on his hips, the friction as the cock slides in and out of him, and the sparks it all sends to his own throbbing dick, where he’s leaking precome onto the ground between his spread feet. 

Then one of the hands on his hips moves, reaches around to wrap around his length and pumps once, twice, before it's all over and Stiles tips over the edge. He arches his back as much as he can, clenches around the cock that's balls deep inside him, and shoots come all over the ground and probably the back of the Jeep. 

He's still trembling with aftershocks when the cock in him moves again, the hand lets go of his dick when Stiles winces from overstimulation. He relaxes as the man fucks in a few more times before he tenses and pushes as deep as he can, the throb of his cock sending little shockwaves through Stiles as he feels the heat pump inside him. 

For a while neither of them move. Stiles doesn't want to, the feeling of fullness everything he ever wanted. But then the cock inside him stars to soften and pulls out slowly, thumbs around his rim easing the glide out. When it's out, the thumbs stay, rubbing on the edges of the stretched rim, the breeze back to blow over Stiles's hole and making him shiver. 

He wonders if he should stay like this, wait until the man leaves, keep the anonymity of their encounter. But before he can make a decision, he's tugged backward and his side nudged. So he awkwardly moves, his knees shaky and unstable, rolling around and pushing himself up, eyes still closed until he's sitting up, feeling a little woozy. 

That's when he finally looks, finally lets his eyelids lift up to see who is standing there, breathing heavily and resting their hands on his shoulders, steadying him. 

"Oh," he breathes out when his eyes land on the familiar abs, then move up until he's looking at a face he knows too well. "Hi." 

"Stiles," Derek says, his voice somewhere between fond and exasperated, like he isn't sure how to feel. 

He had to have known it was Stiles, there's no doubt about it, but he looks like he's fighting regret and embarrassment like he wants to take it back and for nothing to have happened.

"I'm not sorry," Sitles says, not thinking it over too hard. 

It was his first time, he doesn't want to have regrets. He doesn't have any. He doesn't want  _ Derek _ to have any either. 

Derek sighs heavily and moves one hand to Stiles's jaw, cupping it and tilting his face up. 

"Me neither," he says, and the weight that was falling down on Stiles's chest breaks apart. 

He shuffles forward, his knees still unstable as he gets up, and when he's standing he tilts forward until his lips are pressed against Derek's in a kiss that both of them deepen fast. 

**Author's Note:**

> Yo, I'm [on tumblr](http://pleasurific.tumblr.com/) too.


End file.
